5,6-diamino-2',3'-O-isopropylideneuridine | 656808-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,6-diamino-2',3'-O-isopropylideneuridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5,6-diaminopyrimidine-2,4-dione
• CAS: 656808-50-3
• 化学式: C₁₂H₁₈N₄O₆
• 分子量: 314.298
• InChiKey: FHVVHGDOPLJTAV-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4'-二氟苯偶酰 、 5,6-diamino-2',3'-O-isopropylideneuridine 以 乙醇 为溶剂， 反应 18.0h， 以60%的产率得到1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6,7-bis(4-fluorophenyl)pteridine-2,4-dione
  参考文献：
  名称：

  Novel and Facil Synthesis and Evaluation of Antitumor Activities of 6,7-Bisaryl-1-(β-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones

  摘要：

  Novel 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4( 1H,3H)-dione derivatives were synthesized by condensation of 5,6-diamino-2',3'-O-isopropylideneuridine, which was derived from uridine, with an appropriate alpha,beta-diketon, followed by acidic hydrolysis allowing removal of the isopropylidene group of the sugar moiety as a protecting group. Moreover, several N-3 alkyl derivatives of the 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones were obtained by alkylation of the 6,7-bisaryl-l-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones with alkyl halides and by their acidic hydrolysis for deprotection. The antitumor activities of all synthesized compounds against CCRF-HSB-2 and KB cell lines were also investigated in vitro and some of the compounds showed prospective antitumor activities.

  DOI：

  10.3987/com-09-s(s)77
• 作为产物：
  描述：

  6-amino-5-nitroso-2',3'-O-isopropylideneuridine 在 sodium dithionite 、 溶剂黄146 、 氨 作用下， 以 水 为溶剂， 以60%的产率得到5,6-diamino-2',3'-O-isopropylideneuridine
  参考文献：
  名称：

  Novel and Facil Synthesis and Evaluation of Antitumor Activities of 6,7-Bisaryl-1-(β-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones

  摘要：

  Novel 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4( 1H,3H)-dione derivatives were synthesized by condensation of 5,6-diamino-2',3'-O-isopropylideneuridine, which was derived from uridine, with an appropriate alpha,beta-diketon, followed by acidic hydrolysis allowing removal of the isopropylidene group of the sugar moiety as a protecting group. Moreover, several N-3 alkyl derivatives of the 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones were obtained by alkylation of the 6,7-bisaryl-l-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones with alkyl halides and by their acidic hydrolysis for deprotection. The antitumor activities of all synthesized compounds against CCRF-HSB-2 and KB cell lines were also investigated in vitro and some of the compounds showed prospective antitumor activities.

  DOI：

  10.3987/com-09-s(s)77

文献信息

• Novel and Facil Synthesis and Evaluation of Antitumor Activities of 6,7-Bisaryl-1-(β-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones
  作者：Tomohisa Nagamatsu、Rafiya Khan Kandahary、Abugafar M. L. Hossion、Noriyuki Ashida

  DOI：10.3987/com-09-s(s)77

  日期：——

  Novel 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4( 1H,3H)-dione derivatives were synthesized by condensation of 5,6-diamino-2',3'-O-isopropylideneuridine, which was derived from uridine, with an appropriate alpha,beta-diketon, followed by acidic hydrolysis allowing removal of the isopropylidene group of the sugar moiety as a protecting group. Moreover, several N-3 alkyl derivatives of the 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones were obtained by alkylation of the 6,7-bisaryl-l-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones with alkyl halides and by their acidic hydrolysis for deprotection. The antitumor activities of all synthesized compounds against CCRF-HSB-2 and KB cell lines were also investigated in vitro and some of the compounds showed prospective antitumor activities.